And the Cracker Jack kid.
Donald Duck’s is sans pants, of course.
Tunic over bloomers with huge floppy bow tie and big tam o’shanter worn over page boy hairdo: Buster Brown.
Ear Ring - Mr. Clean.

Ascot - Fred on Scooby Doo
Or Mister Furley.
I got one that is both one person and one creative work: the big white suit that David Byrne wore for the video of Once In A Lifetime.

Sneakers and a zip up cardigan - Mr. Rogers.
Specifically, blue Keds.
Round glasses + bowler (+ silk tie and vest or other manly apparel) = Annie Hall/Diane Keaton

Spike heels, black fishnets and a garter belt = **Bettie Page **FTW!
For me, that’s associated with Dr. Frank N. Furter from Rocky Horror Picture Show.
A white headscarf, alone or sometimes under a flat-brimmed western hat, is always going to be associated with Georgia O’Keeffe for me.
Eyepatch (in non-pirate context) - Moshe Dayan.

Eyepatch (in non-pirate context) - Moshe Dayan.
I always associate an eyepatch with author Andrew Vachss
The eyes of Tammy Faye Baker.
Green Hawaiian-type shirt with black pinstripes, black shorts with a white stripe on the side, brown sandals, freckles, unisex bowl haircut - Peppermint Patty.
deleted.
Why hasn’t anyone mentioned a rumpled raincoat yet?

I always associate an eyepatch with author Andrew Vachss
Never heard of him. I guess it’s a matter of cultural context.

Why hasn’t anyone mentioned a rumpled raincoat yet?
“Just one more thing . . . .”
Cat-eyed glasses - Dame Edna Everidge.
What about the famous ear-flapped hunting cap worn by Ignatius J. Reilly?
White disco suit – Tony Manero
Leather Jacket – The Fonz
Yellow jumpsuit and matching athletic shoes – Bruce Lee, or Beatrix Kiddo
This thread is fun.
Big gold chains - Mr. T.
Kangol hat - L.L. Cool J.
White halter dress - Marilyn Monroe
Banana skirt - Josephine Baker
Huge African head wrap - Erycah Badu
Swan Dress - Bjork